The Baylis-Hillman adducts as valuable source for one-pot multi-step synthesis: A facile synthesis of substituted piperidin-2-ones

Helvetica Chimica Acta

Volumn 93, Issue 6, 2010, Pages 1180-1186

  Basavaiah, Deevi ^a   Reddy, Raju Jannapu ^a   Lenin, Dandamudi V ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BAYLIS-HILLMAN ADDUCTS; FACILE SYNTHESIS; JOHNSON-CLAISEN REARRANGEMENTS; ONE-POT MULTI-STEP SYNTHESIS; UNSATURATED NITRILES;

ALDEHYDES; CYANIDES; ETHERS;

CYCLIZATION;

ACRYLONITRILE; ALCOHOL; ALDEHYDE; PIPERIDIN 2 ONE DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 77954156544     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.200900352     Document Type: Article

References (69)

1. D. Basavaiah, D. V. Lenin, B. Devendar, Tetrahedron Lett. 2009, 50, 3538;
2. D. Basavaiah, R. J. Reddy, Org. Biomol. Chem. 2008, 6, 1034;
3. D. Basavaiah, R. J. Reddy, J. Srivardhana Rao, Tetrahedron Lett. 2006, 47, 73;
4. D. Basavaiah, J. Srivardhana Rao, R. J. Reddy, J. Org. Chem. 2004, 69, 7379;
5. D. Basavaiah, D. S. Sharada, A. Veerendhar, Tetrahedron Lett. 2004, 45, 3081;
6. D. Basavaiah, T. Satyanarayana, Chem. Commun. 2004, 32;
7. D. Basavaiah, A. Jaganmohan Rao, Chem. Commun. 2003, 604;
8. D. Basavaiah, A. Jaganmohan Rao, Tetrahedron Lett. 2003, 44, 4365;
9. D. Basavaiah, R. M. Reddy, N. Kumaragurubaran, D. S. Sharada, Tetrahedron 2002, 58, 3693;
10. D. Basavaiah, T. Satyanarayana, Org. Lett. 2001, 3, 3619;
11. D. Basavaiah, M. Bakthadoss, S. Pandiaraju, Chem. Commun. 1998, 1639.
12. S. Kumar, C. Flamant-Robin, Q. Wang, A. Chiaroni, N. A. Sasaki, J. Org. Chem. 2005, 70, 5946;
13. D. S. Middleton, A. R. MacKenzie, S. D. Newman, M. Corless, A. Warren, A. P. Marchington, B. Jones, Bioorg. Med. Chem. Lett. 2005, 15, 3957;
14. T. R. Elworthy, E. R. Brill, C. C. Caires, W. Kim, L. K. Lach, J. L. Tracy, S.-S. Chio, Bioorg. Med. Chem. Lett. 2005, 15, 2523;
15. F. Yokokawa, A. Inaizumi, T. Shioiri, Tetrahedron 2005, 61, 1459;
16. H. K. Lee, J. S. Chun, C. S. Pak, Tetrahedron 2003, 59, 6445;
17. A. R. MacKenzie, A. P. Marchington, D. S. Middleton, S. D. Newman, B. C. Jones, J. Med. Chem. 2002, 45, 5365;
18. L. M. Nogle, T. R. Williamson, W. H. Gerwick, J. Nat. Prod. 2001, 64, 716;
19. N. Yamazki, T. Ito, C. Kibayashi, Tetrahedron Lett. 1999, 40, 739;
20. R. Bonjouklian, T. A. Smitka, A. H. Hunt, J. L. Occolowitz, T. J. Perun Jr., L. Doolin, S. Stevenson, L. Knauss, R. Wijayaratne, S. Szewczyk, G. M. L. Patterson, Tetrahedron 1996, 52, 395.
21. P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953;
22. K. Takasu, N. Nishida, M. Ihara, Synlett 2004, 1844;
23. R. G. Arrayás, A. Alcudia, L. S. Liebeskind, Org. Lett. 2001, 3, 3381;
24. E. Jao, P. B. Slifer, R. Lalancette, S. S. Hall, J. Org. Chem. 1996, 61, 2865;
25. T. Fujji, S. Yoshifuji, Tetrahedron 1970, 26, 5953.
26. C. E. Aroyan, A. Dermenci, S. J. Miller, Tetrahedron 2009, 65, 4069;
27. V. Declerck, J. Martinez, F. Lamaty, Chem. Rev. 2009, 109, 1;
28. V. Singh, S. Batra, Tetrahedron 2008, 64, 4511;
29. D. Basavaiah, K. V. Rao, R. J. Reddy, Chem. Soc. Rev. 2007, 36, 1581;
30. D. Basavaiah, A. Jaganmohan Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811;
31. P. Langer, Angew. Chem., Int. Ed. 2000, 39, 3049;
32. E. Ciganek, in 'Organic Reactions', Ed. L. A. Paquette, Wiley, New York, 1997, Vol. 51, p. 201;
33. D. Basavaiah, P. Dharma Rao, R. Suguna Hyma, Tetrahedron 1996, 52, 8001;
34. S. E. Drewes, G. H. P. Roos, Tetrahedron 1988, 44, 4653.
35. A. Trofimov, V. Gevorgyan, Org. Lett. 2009, 11, 253;
36. E. J. Lenardão, J. de Oliveiros Feijó, S. Thurow, G. Perin, R. G. Jacob, C. C. Silveira, Tetrahedron Lett. 2009, 50, 5215;
37. N. Abermil, G. Masson, J. Zhu, J. Am. Chem. Soc. 2008, 130, 12596;
38. M. Shi, X.-G. Liu, Org. Lett. 2008, 10, 1043;
39. P. Shanmugam, V. Vaithiyanathan, K. Selvakumar, Tetrahedron Lett. 2008, 49, 2119;
40. M. Bakthadoss, N. Sivakumar, G. Sivakumar, G. Murugan, Tetrahedron Lett. 2008, 49, 820;
41. F. C. Pigge, R. Dhanya, E. R. Hefgen, Angew. Chem., Int. Ed. 2007, 46, 2887;
42. S. Chuprakov, D. A. Malyshev, A. Trofimov, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 14868;
43. D. Basavaiah, K. Ramesh Reddy, N. Kumaragurubaran, Nat. Protoc. 2007, 2, 2665;
44. A. Kattuboina, P. Kaur, C. Timmons, G. Li, Org. Lett. 2006, 8, 2771;
45. M. E. Krafft, J. A. Wright, Chem. Commun. 2006, 2977;
46. L. Navarre, S. Darses, J.-P. Genet, Adv. Synth. Catal. 2006, 348, 317;
47. V. Singh, G. P. Yadav, P. R. Maulik, S. Batra, Tetrahedron 2006, 62, 8731;
48. G. W. Kabalka, B. Venkataiah, C. Chen, Tetrahedron Lett. 2006, 47, 4187;
49. J. Srivardhana Rao, J.-F. Brière, P. Metzner, D. Basavaiah, Tetrahedron Lett. 2006, 47, 3553;
50. M. Dadwal, R. Mohan, D. Panda, S. M. Mobin, I. N. N. Namboothiri, Chem. Commun. 2006, 338;
51. S. C. Kim, S. Gowrisankar, J. N. Kim, Tetrahedron Lett. 2006, 47, 3463;
52. P. V. Ramachandran, S. Madhi, L. Bland-Berry, M. V. R. Reddy, M. J. O'Donnell, J. Am. Chem. Soc. 2005, 127, 13450;
53. M. Shi, L.-H. Chen, C.-Q. Li, J. Am. Chem. Soc. 2005, 127, 3790;
54. K. Matsui, S. Takizawa, H. Sasai, J. Am. Chem. Soc. 2005, 127, 3680;
55. T. Turki, J. Villiéras, H. Amri, Tetrahedron Lett. 2005, 46, 3071;
56. L. S. Santos, C. H. Pavam, W. P. Almeida, F. Coelho, M. N. Eberlin, Angew. Chem., Int. Ed. 2004, 43, 4330;
57. D. Basavaiah, A. K. D. Bhavani, S. Pandiaraju, P. K. S. Sarma, Synlett 1995, 243;
58. D. Basavaiah, S. Pandiaraju, P. K. S. Sarma, Tetrahedron Lett. 1994, 35, 4227;
59. D. Basavaiah, V. V. L. Gowriswari, P. K. S. Sarma, P. Dharma Rao, Tetrahedron Lett. 1990, 31, 1621.
60. A. M. M. Castro, Chem. Rev. 2004, 104, 2939;
61. P. Wipf, in 'Comprehensive Organic Synthesis', Eds. B. M. Trost, I. Fleming, L. Paquette, Pergamon Press, New York, 1990, Vol. 5, p. 827;
62. W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Brocksom, T.-T. Li, D. J. Faulkner, M. R. Petersen, J. Am. Chem. Soc. 1970, 92, 741.
63. a) D. Basavaiah, S. Pandiaraju, Tetrahedron Lett. 1995, 36, 757;
64. b) D. Basavaiah, S. Pandiaraju, M. Krishnamacharyulu, Synlett 1996, 747;
65. c) B. Das, A. Majhi, J. Banerjee, Tetrahedron Lett. 2006, 47, 7619.
66. J. O. Osby, S. W. Heinzman, B. Ganem, J. Am. Chem. Soc. 1986, 108, 67;
67. S. W. Heinzman, B. Ganem, J. Am. Chem. Soc. 1982, 104, 6801;
68. T. Satoh, S. Suzuki, Y. Suzuki, Y. Miyaji, Z. Imai, Tetrahedron Lett. 1969, 10, 4555.
69. D. Basavaiah, V. V. L. Gowriswari, Synth. Commun. 1987, 17, 587.